Recent methods for the synthesis of (E)-alkene units in macrocyclic natural products

Abstract : (E)-Alkene units are frequently found in macrocyclic natural products. Among the reactions that form the double bond during the cyclization, the classical Horner-Emmons coupling is still frequently used with success. During the last decade, ring-closing metathesis has emerged as a very powerful tool for the synthesis of large rings, but the E/Z selectivity, which is rarely predictable, depends on many factors which will be discussed in this review. The best solution might be a two-step procedure involving ring-closing alkyne metathesis (RCAM) followed by stereoselective reduction of the macrocyclic alkyne unit to the corresponding E double bond.
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Joëlle Prunet. Recent methods for the synthesis of (E)-alkene units in macrocyclic natural products. Angewandte Chemie International Edition, Wiley-VCH Verlag, 2003, 42 (25), pp.2826-2830. ⟨10.1002/anie.200301628⟩. ⟨hal-00954916⟩

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